N,N-dimethylformamide

• ChemBase编号: 1614
• 分子式: C3H7NO
• 平均质量: 73.09378
• 单一同位素质量: 73.05276385
• SMILES: CN(C)C=O
• Canonical SMILES: O=CN(C)C
• InChI: InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
• InChIKey: ZMXDDKWLCZADIW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N,N-dimethylformamide
• IUPAC传统名: dimethylformamide
• 别名: N,N-二甲基甲酰胺, 无水; N,N-二甲基甲酰胺, 无水, 无氨; N,N-二甲基甲酰胺, ACS; N,N-二甲基甲酰胺, 光谱级; N,N-二甲基甲酰胺, HPLC级; N,N-二甲基甲酰胺; N,N-二甲基甲酰胺, HPLC 级; N,N-Dimethylformamide, anhydrous; N,N-Dimethylformamide, anhydrous, amine free; N,N-Dimethylformamide, ACS; N,N-Dimethylformamide, Spectrophotometric Grade; N,N-Dimethylformamide, HPLC Grade; N,N-Dimethylmethanamide; Dimethylformamide; DMF; N-Formyldimethylamine; N,N-Dimethylformamide 99.8%; N,N-Dimethylformamide; N,N-DIMETHYLFORMAMIDE, HPLC/SPECTRO GRADE; N,N-DIMETHYLFORMAMIDE, ANHYDROSOLV GRADE; N,N-DIMETHYLFORMAMIDE, BIO GRADE; N,N-DIMETHYLFORMAMIDE; NCI-c60913; N,N-DIMETHYLFORMAMIDE ACS REAGENT GRADE; N,N-DIMETHYL FORMAMIDE

登记号

• CAS号: 68-12-2
• EC号: 200-679-5
• MDL号: MFCD00003284
• Beilstein号: 605365
• 默克索引号: 143243
• PubChem SID: 46506036; 24849438; 24878402; 24865091; 24886401; 24872907; 160965071; 24853607; 24849479; 24867912; 24893883; 24865086; 24859200; 24867382; 24883591; 24856379; 24859940
• PubChem CID: 6228
• CHEBI ID: 17741
• CHEMBL: 268291
• Chemspider ID: 5993
• DrugBank ID: DB01844
• KEGG ID: C03134
• 医学主题词(MeSH): Dimethylformamide
• 美国药典/FDA物质标识码: 8696NH0Y2X
• 维基百科标题: Dimethylformamide

理论计算性质

JChem

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): -0.63163495
• LogD (pH = 7.4): -0.6316349
• Log P: -0.6316349
• 摩尔折射率: 19.7688 cm^3
• 极化性: 7.48225 Å^3
• 极化表面积: 20.31 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.77
• LOG S: 1.0
• 溶解度: 7.25e+02 g/l

分子性质

理化性质

• 溶解度: 1000 mg/mL at 25 oC [ISHOW (NA--) @2ND]; Miscible in water
• 外观: APHA: ≤15; clear; Colourless liquid; Liquid
• 熔点: -60.45°C (212.7K); -60.5 °C; -61 °C(lit.); -61°C; -61°C
• 沸点: 151.85 - 153.85°C (425 - 427 K); 152 - 153 °C; 152-154 °C; 153 °C(lit.); 153°C; 153°C
• 闪点: 136.4 °F; 57°C(135°F); 58 °C (closed cup and DIN 51755); 58 °C; 58°C
• 自燃点: 410 °C (DIN 51794); 445 °C; 833 °F
• 密度: .94 g/cm^3 at 20 °C; 0.944; 0.944 g/mL(lit.); 0.948 g mL^-1; 0.948 g/mL at 20 °C; 0.948-0.950 g/mL at 20 °C
• 折射率: 1.4305 (at 20 °C); 1.431; 1.4310; n20/D 1.4290-1.4310; n20/D 1.430; n20/D 1.430(lit.); n20/D 1.431
• 蒸汽压: .035 hPa at 20 °C; 2.7 mmHg ( 20 °C); 516 Pa
• 蒸汽密度: 2.5 (vs air); 2.51 (air = 1)
• 分配系数: -0.829
• 紫外吸收波长: 270 nm; λ: 270 nm Amax: 1.00; λ: 275 nm Amax: 0.30; λ: 280 nm Amax: 0.25; λ: 290 nm Amax: 0.14; λ: 295 nm Amax: 0.10; λ: 300 nm Amax: 0.1; λ: 310 nm Amax: 0.05; λ: 320 nm Amax: 0.03; λ: 340 nm Amax: 0.005; λ: 340-400 nm Amax: 0.01
• 疏水性(logP): -1.01 [HANSCH,C ET AL. (1995)]
• 粘度: 0.92 mPa s (at 20 °C)
• 气味: fishy, ammoniacal
• 热容: 146.05 J K^-1 mol^-1
• 标准摩尔燃烧焓 (ΔcH^o298): -1.9428–-1.9404 MJ mol^-1
• 标准摩尔生成焓 (ΔfH^o298): -240.6–-238.2 kJ mol^-1
• 吸光度: 1.00
• 透光率: 270 nm, ≥20%; 280 nm, ≥70%; 300 nm, ≥90%; 310 nm, ≥89.2%; 330 nm, ≥98%

安全信息

• 保存条件: Room Temperature (15-30°C); Room Temperature (15-30°C), Avoid excess heat
• 保存注意事项: Flammable/Harmful/Irritant/Teratogenic/Store under Argon; Hygroscopic
• RTECS编号: LQ2100000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有毒(Toxic) (T)
• 联合国危险货物编号: 2265; UN2265
• 德国WGK号: 1
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 3; III
• 澳大利亚Hazchem: 2W
• 危险公开号: 61-20/21-36; R:10-20/21-36-61; r61, r20/21, r36
• 安全公开号: 53-45; S:16-45-53; s45
• 欧盟危险货物分类: F1
• 欧盟危险识别号(EUHIN): 3B
• 美国ERG指导号: 129
• TSCA收录: 是
• 欧盟危险品索引: 616-001-00-X
• GHS危险品标识: GHS exclamation mark; GHS flame; GHS health hazard; GHS02; GHS07; GHS08
• GHS警示词: DANGER; Danger
• NFPA704:
  

  2

  2

  0
• 半数致死量: 1.5 g kg^-1 (dermal, rabbit); 2.8 g kg^-1 (oral, rat)
• 爆炸极限: 15.2 %; 2.2–15.2%
• GHS危险声明: 226, 312, 319, 332, 360; H226-H312 + H332-H319-H360D; H226-H312-H319-H332-H360D; H360-H226-H312-H332-H319
• GHS警示性声明: 280, 305+351+338, 308+313; P201-P280-P305 + P351 + P338-P308 + P313; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2265 3/PG 3

产品相关信息

• 纯度: ≥99%; ~99%; ≥98.0% (GC); ≥99%; ≥99% (GC); ≥99.0%; ≥99.5%; ≥99.5% (GC); ≥99.8%; ≥99.8% (GC); ≥99.9%; ≥99.9% (GC); 99%; 99.7+%; 99.8%; 99.8+%; 99.9%
• 级别: absolute; ACS; ACS reagent; ACS spectrophotometric grade; analytical standard; anhydrous; B&J Brand (product of Burdick & Jackson); biotech. grade; CHROMASOLV® Plus; for HPLC; for molecular biology; for peptide synthesis; for residue analysis; for UV-spectroscopy; HPLC; JIS special grade; puriss.; puriss. p.a.; purum; REAGENT; ReagentPlus®; SAJ first grade; SPECTRANAL™
• 包装: ampule of 1000 mg; packaged under Argon in resealable ChemSeal? bottles
• 适用性: GC-Headspace tested; passes test for IR spectroscopy; passes test for suitability for UV spectroscopy; suitable for neutral marker for measuring electroosmotic flow (EOF); suitable for solvent for chromogenic substrates (X-Gal, etc.) used in molecular biology applications.
• 蒸发残渣: <0.0005%; ≤0.0005%; ≤0.005%
• 杂质: <0.005% water; <8 ppm Free amines as dimethylamine; ≤0.0005 meq/g Titr. acid; ≤0.001% non-volatile matter; ≤0.003 meq/g Titr. base; ≤0.003% free acid (as CH3COOH); ≤0.003% Free acid (as CH3COOH); ≤0.005% free alkali (as NH3); ≤0.005% Free alkali (as NH3); ≤0.030% water; ≤0.05% water; ≤0.05% water (Karl Fischer); ≤0.08% water (Karl Fischer); ≤0.1% Water (Karl Fischer); ≤0.1% water (Karl Fischer); ≤0.15% water; ≤1 ppb fluorescence (quinine) at 254 nm; ≤1 ppb fluorescence (quinine) at 365 nm; ≤5 ng/L suitability for residue analysis
• 痕量阳离子: Al: ≤0.5 mg/kg; B: ≤0.02 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Li: ≥0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤1 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sn: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.1 mg/kg; Zn: ≤0.2 mg/kg
• 有效期: (limited shelf life, expiry date on the label)
• 提纯方法: glass distillation
• 品质说明: for pesticide residue analysis; over molecular sieve (H2O ≤0.005%); over molecular sieve (H2O ≤0.01%)
• λ: 1 cm path, H2O reference; H2O reference
• abs.: /270 nm 1.00; /275 nm 0.30; /295 nm 0.10; /310 nm 0.05; /340 nm 0.010; /400 nm 0.010
• Appearance: APHA: ≤15
• 线性分子式: HCON(CH3)2

详细说明

MP Biomedicals - 02195147

1 ml = ~0.94 g

MP Biomedicals - 02191417

ACS Reagent Grade
Specific Gravity: 0.944 g/ml
b.p. 152-154°C
Clear, liquid

MP Biomedicals - 02194818

Molecular Biology Reagent
Purity: 99+%
A solvent for chromogenic substrates in molecular biology experiments.

Sigma Aldrich - D8300

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - 539465

Application
多种疏水性有机化合物的溶剂。
法律信息
AldraSORB is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 34489

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - 40250

Application
多种疏水性有机化合物的溶剂。
Other Notes
可能实行销售限制

Sigma Aldrich - 40245

Application
多种疏水性有机化合物的溶剂。
General description
可以成本价获得专用手册 (85475)。
Other Notes
可能实行销售限制

Sigma Aldrich - 40249

Application
多种疏水性有机化合物的溶剂。
Other Notes
可能实行销售限制
包装
tri Q-Multi-way 桶（详细信息请见附录）

Sigma Aldrich - 30576

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - D4551

Application
多种疏水性有机化合物的溶剂。
包装
250, 500 mL in glass bottle

Sigma Aldrich - 40240

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - 51781

Application
多种疏水性有机化合物的溶剂。
General description
Watch a 6-minute presentation that demonstrates the effective use of our High Purity Solvents for GC Headspace Analysis
Suitability
针对 GC-HS 进行了测试
Protocols & Applications
The Utility of Headspace Grade Solvents for the Analysis of Organic Volatile Impurities

Sigma Aldrich - 40243

Application
多种疏水性有机化合物的溶剂。
General description
在 GC/ECD 从林丹到 DDT 的保留时间范围内，不会有信号强度高于 5ng/l 林丹的杂质存在

Sigma Aldrich - 227056

Application
多种疏水性有机化合物的溶剂。
包装
1, 6×1, 2, 4×2 L in Sure/Seal™
View returnable container options.
100, 12×100 mL in Sure/Seal™
18, 200 L in Pure-Pac™ 1

Sigma Aldrich - 33120

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - 07-4430

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - D158550

Application
多种疏水性有机化合物的溶剂。
包装
1, 6×1, 4×2.5, 4 L in poly bottle
5 L in poly drum
20 L in steel drum
Legal Information
DuPont 产品
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 07-4440

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - 72438

Application
多种疏水性有机化合物的溶剂。

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Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - 648531

Application
多种疏水性有机化合物的溶剂。
包装
4×4 L in PVC coated
带聚合物涂层瓶包装
法律信息
CHROMASOLV 注册商标 Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 494488

Application
多种疏水性有机化合物的溶剂。
包装
1, 6×1, 2 L in Sure/Seal™
10 L in ss drum
10L 密封不锈钢桶包装；18L、56L、200L Pure-pac® 不锈钢容器包装；1L、2L Sure/seal™ 瓶包装
18 L in Pure-Pac™ 1
20 L in Nowpak™ II
View returnable container options.
56, 200, 400 L in Pure-Pac™ 1
法律信息
Pure-Pac 注册商标 Sigma-Aldrich Co. LLC
Sure/Seal 商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 270547

Application
多种疏水性有机化合物的溶剂。
包装
1, 6×1, 2, 4×2, 4×4 L in glass bottle
10 L in ss drum
10L 密封不锈钢桶包装；100mL、1L、2L、6×1L、4×2L、4×4L 玻璃瓶包装
100 mL in glass bottle
200 L in Pure-Pac™ 1
法律信息
CHROMASOLV 注册商标 Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 40246

Application
多种疏水性有机化合物的溶剂。
General description
可以成本价获得专用手册 (85475)。
Other Notes
可能实行销售限制

Sigma Aldrich - 34903

Application
多种疏水性有机化合物的溶剂。
法律信息
SPECTRANAL 商标 Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 442568

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - 437573

Application
多种疏水性有机化合物的溶剂。
包装
18 L in VerSA-Flow™
4×4 L in PVC coated
4×4L 带聚合物涂层瓶包装；18L VerSA-Flow® 容器包装
法律信息
Pure-Pac 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 319937

Application
多种疏水性有机化合物的溶剂。
包装
1, 6×1, 2, 2.5, 4, 4×4 L in glass bottle
20 L in steel drum
200 L in poly drum
500, 6×500 mL in glass bottle

Sigma Aldrich - 15440

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - 154814

Application
多种疏水性有机化合物的溶剂。
包装
1, 6×1, 4×4 L in glass bottle

Sigma Aldrich - 40255

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - 40228

Application
多种疏水性有机化合物的溶剂。

DrugBank - DB01844

• Drug Groups: experimental
• References: Redlich CA, Beckett WS, Sparer J, Barwick KW, Riely CA, Miller H, Sigal SL, Shalat SL, Cullen MR: Liver disease associated with occupational exposure to the solvent dimethylformamide. Ann Intern Med. 1988 May;108(5):680-6. [Pubmed]
• External Links: Wikipedia

Apollo Scientific Ltd - OR16840

For Peptide Synthesis

参考文献

• Redlich CA, Beckett WS, Sparer J, Barwick KW, Riely CA, Miller H, Sigal SL, Shalat SL, Cullen MR: Liver disease associated with occupational exposure to the solvent dimethylformamide. Ann Intern Med. 1988 May;108(5):680-6. Pubmed
• Dipolar aprotic solvent, in which anions have enhanced nucleophilicity, compare Dimethyl sulfoxide, A13280. Effective solvent for a vast range of reactions.
• In combination with POCl₃, (COCl)₂, etc., generates an iminium chloride intermediate for the formylation of reactive aromatic nuclei by the Vilsmeier reaction:
  
• Compare also N-Methylformanilide, A11829, and preformed Vilsmeier reagent (Chloromethylene)dimethylammonium chloride, B24172. Monograph: Synthesis Using Vilsmeier Reagents, C. M. Marson, P. R. Giles, CRC Press, Boca Raton, FL (1994). Formylation can be extended to less active substrates, e.g. acenaphthene or mesitylene, with the DMF-triflic anhydride reagent: J. Chem. Soc., Chem. Commun., 1571 (1990). Under Vilsmeier conditions, electron-rich alkenes can be converted to ɑ?-unsaturated aldehydes; see, e.g.: Synthesis, 752 (1976); and ketones to ?-chloroenals: Synthesis, 496 (1985); Org. Synth. Coll., 5, 215 (1973).
• Vilsmeier conditions also promote dehydrations, e.g. in cyclodehydration of hydroxyphenols to give cyclic ethers, as an efficient alternative to the Mitsunobu reaction: J. Chem. Soc., Perkin 1, 2249 (1996); J. Org. Chem., 59, 4346 (1994):
  
• CAUTION! Thermal runaway reactions can occur with NaH; see Sodium hydride, 13431.
• DMF can also be used for formylation with alkyllithium or Grignard reagents: Synthesis, 228 (1984).
• In aqueous DMF, tosylate esters undergo formolysis to formate esters: Synth. Commun., 26, 1031 (1996).
• For the free-radical formylation of perfluoroalkyl iodides, see Zinc-copper couple, L09811.