重氮甲烷
重氮甲烷用途
1、重氮甲烷是一种常用的甲基化试剂，常用于羧酸、醇、酚以及酰胺等官能团的甲基化。另外，该试剂也可用于合成重氮酮或环丙烷类衍生物。
杂原子的甲基化 重氮甲烷常用在羧酸类化合物的甲基化反应中，在反应过程中羧酸提供质子使重氮甲烷的亚甲基质子化而形成重氮羧酸酯，然后发生类似SN2的反应而生成羧酸酯 (式1)。在该反应中无须加入其它的催化剂如路易斯酸等，因此这种条件下其它的基团如醇、烯键等则不会发生改变。
重氮甲烷也能使酚羟基甲基化，例如在乙醚和醇溶液中，重氮甲烷能使酪氨酸的酚羟基定量地甲基化 (式2)。
除此之外，重氮甲烷可以选择性地甲基化异羟肟酸 (式3)，当R为脂肪基时，甲基化发生在含氧原子的位置；当R为芳香基时，NH和OH是竞争性的亲核位点。在一定的条件下，以烯醇形式存在的酰胺与重氮甲烷反应时可以形成N,O-二甲基化化合物。
α-重氮酮的合成 重氮甲烷与酰卤试剂作用可生成α-重氮酮。该重氮酮是一种比较重要的有机中间体化合物，可进一步反应生成环状化合物，或与醛类反应而使碳链得到延长等 (式4)。重氮甲烷也可以在PPh3-NBS试剂存在下，使羧酸类化合物变为α-重氮酮 (式5)。
加成反应 重氮甲烷可与酮发生加成反应(式6)，生成扩环产物；也可与不饱和双键化合物发生环加成反应。用价键理论和计算模型可以详细的解释它与乙烯的1,3-二偶极加成反应的机理。对于一些含有双键的金属有机化合物，重氮甲烷还可以与之反应构成三元环 (式7)。
2.用于有机合成。
重氮甲烷名称
[ CAS 号 ]:
334-88-3
[ 中文名 ]:
重氮甲烷
[ 英文名 ]:
Diazomethane
[中文别名 ]:
[英文别名 ]:
- Methane,diazo
- Acomethylene
- Azimethylene
- Diazirine
- Diazonium methylide
- EINECS 206-382-7
重氮甲烷物理化学性质
[ 熔点 ]:
-145ºC
[ 分子式 ]:
CH2N2
[ 分子量 ]:
42.04000
[ 精确质量 ]:
42.02180
[ PSA ]:
37.39000
[ 折射率 ]:
1.684
[ 储存条件 ]:
轻装轻放,库房通风、远离明火、高温、阳光,与氧化剂、易燃物,食品原料分开存放
重氮甲烷MSDS
重氮甲烷毒性和生态
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- PA7000000
- CHEMICAL NAME :
- Methane, diazo-
- CAS REGISTRY NUMBER :
- 334-88-3
- BEILSTEIN REFERENCE NO. :
- 0102415
- LAST UPDATED :
- 199712
- DATA ITEMS CITED :
- 34
- MOLECULAR FORMULA :
- C-H2-N2
- MOLECULAR WEIGHT :
- 42.05
- WISWESSER LINE NOTATION :
- NNU1
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- LC50 - Lethal concentration, 50 percent kill
- ROUTE OF EXPOSURE :
- Inhalation
- SPECIES OBSERVED :
- Mammal - cat
- DOSE/DURATION :
- 175 ppm/10M
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TCLo - Lowest published toxic concentration
- ROUTE OF EXPOSURE :
- Inhalation
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 272 mg/m3/26W-I
- TOXIC EFFECTS :
- Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors
- TYPE OF TEST :
- TCLo - Lowest published toxic concentration
- ROUTE OF EXPOSURE :
- Inhalation
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 272 mg/m3/26W-I
- TOXIC EFFECTS :
- Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 48 gm/kg/52W-I
- TOXIC EFFECTS :
- Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors
MUTATION DATA
- TYPE OF TEST :
- Mutation in microorganisms
- TEST SYSTEM :
- Mold - Neurospora crassa
- REFERENCE :
- HEREAY Hereditas (Lund, Sweden). (Gjoerloffsgatan 121, S-261 34 Landskrona, Sweden) V.1- 1947- Volume(issue)/page/year: 35,521,1949 *** REVIEWS *** ACGIH TLV-Suspected human carcinogen DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 ACGIH TLV-TWA 0.34 mg/m3 (0.2 ppm) DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 7,223,1974 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 7,223,1974 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 *** U.S. STANDARDS AND REGULATIONS *** MSHA STANDARD-air:TWA 0.2 ppm (0.4 mg/m3) DTLWS* "Documentation of the Threshold Limit Values for Substances in Workroom Air," Supplements. For publisher information, see 85INA8. Volume(issue)/page/year: 3,15,1973 OSHA PEL (Gen Indu):8H TWA 0.2 ppm (0.4 mg/m3) CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1910.1000,1994 OSHA PEL (Construc):8H TWA 0.2 ppm (0.4 mg/m3) CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1926.55,1994 OSHA PEL (Shipyard):8H TWA 0.2 ppm (0.4 mg/m3) CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1915.1000,1993 OSHA PEL (Fed Cont):8H TWA 0.2 ppm (0.4 mg/m3) CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 41,50-204.50,1994 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-AUSTRALIA:TWA 0.2 ppm (0.4 mg/m3);Carcinogen JAN 1993 OEL-DENMARK:TWA 0.1 mg/m3;STEL 0.2 mg/m3 JAN 1993 OEL-FINLAND:TWA 0.2 ppm (0.4 mg/m3) JAN 1993 OEL-FRANCE:TWA 0.2 ppm (0.4 mg/m3) JAN 1993 OEL-GERMANY:TWA 0.2 ppm (0.3 mg/m3);STEL 0.6 ppm (1.0 mg/m3);Carcinogen JAN 1993 OEL-HUNGARY;Carcinogen JAN 1993 OEL-INDIA:STEL 0.4 mg/m3;Skin JAN 1993 OEL-THE NETHERLANDS:TWA 0.2 ppm (0.4 mg/m3) JAN 1993 OEL-RUSSIA:TWA 0.2 ppm (0.4 mg/m3) JAN 1993 OEL-SWITZERLAND:TWA 0.2 ppm (0.35 mg/m3);Carcinogen JAN 1993 OEL-UNITED KINGDOM:TWA 0.2 ppm (0.4 mg/m3) JAN 1993 OEL IN BULGARIA, COLOMBIA, JORDAN, KOREA check ACGIH TLV OEL IN NEW ZEALAND, SINGAPORE, VIETNAM check ACGIH TLV *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH RECOMMENDED EXPOSURE LEVEL (REL) : NIOSH REL TO DIAZOMETHANE-air:10H TWA 0.2 ppm REFERENCE : NIOSH* National Institute for Occupational Safety and Health, U.S. Dept. of Health, Education, and Welfare, Reports and Memoranda. Volume(issue)/page/year: DHHS #92-100,1992 NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 23370 No. of Facilities: 18 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 234 (estimated)
重氮甲烷安全信息
[ 危害码 (欧洲) ]:
Xi,Xn
[ 风险声明 (欧洲) ]:
45
[ 安全声明 (欧洲) ]:
53-45
[ 危险品运输编码 ]:
1953
[ WGK德国 ]:
3
[ 危险类别 ]:
2.3
重氮甲烷制备
该试剂通常是由N-甲基-N-亚硝基胺分解而制备的，最常用的是利用N-甲基-N-亚硝基-对甲苯磺酰胺、1-甲基-3-硝基-1-亚硝基胍或N-甲基-N-亚硝基脲作为原料制备而成。
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