tert-Butyl nitrite

Base Information

• Chemical Name: tert-Butyl nitrite
• CAS No.: 540-80-7
• Molecular Formula: C4H9NO2
• Molecular Weight: 103.121
• Hs Code.: 29209085
• European Community (EC) Number: 208-757-0
• UNII: 4780H7U8LU
• DSSTox Substance ID: DTXSID10202316
• Nikkaji Number: J6.388F
• Wikipedia: Tert-Butyl_nitrite
• Wikidata: Q27259029
• Mol file: 540-80-7.mol

Synonyms:tert-Butyl nitrite;540-80-7;t-Butyl nitrite;1,1-Dimethylethyl nitrite;Nitrous acid, 1,1-dimethylethyl ester;Nitrous Acid tert-Butyl Ester;CCRIS 2098;alpha,alpha-Dimethylethyl nitrite;NITROUS ACID, t-BUTYL ESTER;EINECS 208-757-0;BRN 1209339;(CH3)3CONO;UNII-4780H7U8LU;4780H7U8LU;.alpha.,.alpha.-Dimethylethyl nitrite;Nitrous acid 1,1-dimethyl ethyl ester;tert-butylnitrite;4-01-00-01622 (Beilstein Handbook Reference);t-butylnitrite;t-Butyinitrite;t-butyl-nitrite;tert-butylnitrit;tert.butylnitrite;tertbutyl nitrite;ter-butyl nitrite;tert butyl nitrite;tert-butyl-nitrite;tert.-butylnitrite;tert.butyl nitrite;tert. butyl nitrite;tert.-butyl nitrite;tertiarybutyl nitrite;tertiary butyl nitrite;Tertiary-butyl nitrite;2-methyl2-propyl nitrite;tert-Butyl nitrite, 90%;tert-Butyl nitrite, 96%;2-methyl-2-propyl nitrite;SCHEMBL27393;TERT-BUTYL NITRITE [MI];IOGXOCVLYRDXLW-UHFFFAOYSA-;AMY4009;DTXSID10202316;BCP25945;MFCD00002055;AKOS000121071;NITROUS ACID, TERT-BUTYL ESTER;GS-3770;LS-96767;2-BIPHENYL-3,5-DIFLUORO-ACETICACID;FT-0632348;N0357;EN300-23831;tert-Butyl nitrite, technical, >=90% (GC);D78334;A829951;J-802290;Q-201796;Q27259029;F0001-1416

Chemical Property of tert-Butyl nitrite

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 183mmHg at 25°C
• Refractive Index: n20/D 1.368(lit.)
• Boiling Point: 63.498 °C at 760 mmHg
• Flash Point: ?10 °F
• PSA: 38.66000
• Density: 0.958 g/cm³
• LogP: 1.48290
• Storage Temp.: 2-8°C
• Solubility.: alcohol: very soluble(lit.)
• Water Solubility.: slightly soluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 103.063328530
• Heavy Atom Count: 7
• Complexity: 64.6

Purity/Quality:

98% ^*data from raw suppliers

1,1-DimethylethylNitrite(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xn
• Hazard Codes: F,Xn
• Statements: 11-20/22
• Safety Statements: 16-24-46

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrates and Nitrites
• Canonical SMILES: CC(C)(C)ON=O
• Uses: tert-Butyl nitrite is employed as a reagent for diazotization and nitrosation of alcohols, thiols, amines and cycloalkanes. It plays an important role in photocatalyzed conversion of aryl and heteroarylamines to selenides. It finds application in the preparation of aryl azides from aryl amines. It is also useful for radical multifunctionalization reactions of aliphatic alkenes and source of nitric oxide.

Technology Process of tert-Butyl nitrite

There total 21 articles about tert-Butyl nitrite which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

tert-butyl alcohol (75-65-0) → tert.-butylnitrite (540-80-7)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; at -10 ℃; for 0.0777778h;

Reference yield: 88.0%

t-butoxymethylbenzene (3459-80-1) → tert.-butylnitrite (540-80-7) + tert-butyl nitrate (926-05-6) + benzaldehyde (100-52-7)

Guidance literature:

With nitric acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/ejoc.200390090

Reference yield: 71.0%

[Cl2NNF6]Cu(κ2-O2N)*THF + tert-butyl alcohol (75-65-0) → tert.-butylnitrite (540-80-7) + {[Cl2NNF6]Cu}2(μ-hydroxo)2

Guidance literature:

In benzene-d6; for 8h; Concentration;

DOI:10.1021/jacs.6bll332

upstream raw materials:

tertiary butyl chloride

t-butyl bromide

glycerine trinitrite

tert-butyl alcohol

Downstream raw materials:

isoquinoline-1-carbaldehyde

isoquinoline-1-carbaldehyde-oxime

p-nitroacetophenone oxime

1-(2-nitro-phenyl)-ethanone oxime

Refernces

• 1、 Chen, Peter,Colson, Stephen D.,Chupka, William A.,Berson, Jerome A.. "Flash Pyrolytic Production of Rotationally Cold Free Radicals in a Supersonic Jet. Resonant Multiphoton Spectrum of the 3p2A2''= X2A2'' Origin Band of CH3". . p. 2319 - 2321. Retrieved 1986.
• 2、 Sexto, Alexia,Iglesias, Emilia. "S-Nitrosocaptopril formation in aqueous acid and basic medium. A vasodilator and angiotensin converting enzyme inhibitor". . p. 7207 - 7216. Retrieved 2011.
• 3、 Crookes, Michael J.,Williams, D. Lyn H.. "Rate-limiting NO+ Formation in Nitrosation Reaction in Acetonitrile". . p. 571 - 572. Retrieved 1988.
• 4、 Gao, Yu,Peng, Shan-Qing,Liu, De-Yong,Rui, Pei-Xin,Hu, Xiang-Guo. "Copper-Catalyzed Four-Component Reaction for the Synthesis of N-Difluoroethyl Imides". . p. 1715 - 1721. Retrieved 2019.
• 5、 Dai, Peng-Fei,Wang, Yi-Ping,Qu, Jian-Ping,Kang, Yan-Biao. "tert-Butyl Nitrite as a Twofold Hydrogen Abstractor for Dehydrogenative Coupling of Aldehydes with N-Hydroxyimides". supporting information. p. 9360 - 9364. Retrieved 2021/12/09.