Methyleneaminoacetonitrile

Base Information

• Chemical Name: Methyleneaminoacetonitrile
• CAS No.: 109-82-0
• Molecular Formula: C3H4N2
• Molecular Weight: 68.0782
• Hs Code.: 2926909090
• European Community (EC) Number: 203-709-5
• NSC Number: 128385,57883,3486
• UNII: VUC4O8Q6RO
• DSSTox Substance ID: DTXSID0059378
• Nikkaji Number: J10.595C
• Wikidata: Q27292022
• Mol file: 109-82-0.mol

Synonyms:109-82-0;Methyleneaminoacetonitrile;Methylenaminoacetonitrile;MAAN;Acetonitrile, (methyleneamino)-;2-(methyleneamino)acetonitrile;2-(methylideneamino)acetonitrile;GLYCINONITRILE, N-METHYLENE-;(methyleneamino)acetonitrile;Methyleniminoacetonitrile;N-Methyleneglycinonitrile;(Methylenamino)acetonitrile;USAF DO-5;alpha-Hydroformamine cyanide;Methyleneiminoacetonitrile;N-Methylene glycinonitrile;Methylene aminoacetonitrile;EINECS 203-709-5;UNII-VUC4O8Q6RO;VUC4O8Q6RO;NSC 128385;BRN 1848155;AI3-17751;C3H4N2;NSC-3486;NSC-57883;NSC-128385;WLN: NC1NU1;(methylideneamino)acetonitrile;.alpha.-Hydroformamine cyanide;Methyleneglycinonitrile;Methylenaminoacetonitril;Methyleneamino-acetonitrile;DTXSID0059378;N-METHYLENE-GLYCINONITRILE;NSC3486;Acetonitrile, 2-(methyleneamino)-;AMY24166;NSC57883;(METHYL ENEAMINO)ACETONITRILE;BBL027363;MFCD00001889;NSC128385;STL373466;AKOS009157437;LS-72897;2-(METHYLENEAMINO)ACETONITRILE [MI];FT-0628876;M0212;EN300-42036;W-108704;Q27292022;Z425450894

Chemical Property of Methyleneaminoacetonitrile

Chemical Property:

• Appearance/Colour: White crystals
• Vapor Pressure: 3.71mmHg at 25°C
• Melting Point: 127-130 °C
• Refractive Index: 1.437
• Boiling Point: 151.2 °C at 760 mmHg
• PKA: 3.30±0.50(Predicted)
• Flash Point: 45.2 °C
• PSA: 36.15000
• Density: 0.84 g/cm³
• LogP: 0.21058
• Solubility.: slightly sol. in Benzene
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 68.037448136
• Heavy Atom Count: 5
• Complexity: 66.2

Purity/Quality:

99% ^*data from raw suppliers

Methylenaminoacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=NCC#N
• Description: Methyleneaminoacetonitrile (MAAN) consists of acetonitrile (single bondCtriple bondN) and double bond (single bondNdouble bondC) moieties. It has a high nitrogen content (41.18%) and can be found as chloride and bisulfate salts. MAAN is unstable at room temperature and is usually found as chloride and bisulfate salts.
• Uses and Mechanism of Action: Chemical Intermediate: ; Methyleneaminoacetonitrile (MAAN) serves as an important intermediate in organic synthesis, particularly in the production of carbon materials containing heteroatomic nitrogen.^[1][2]; ; Lathyrogenic Agent: ; Methyleneaminoacetonitrile (MAAN) can affect the growth and synthesis of chondroitin sulfate in embryonic chick tibiotarsi in organ culture.^[2]
• Production Methods: Methyleneaminoacetonitrile (MAAN) can be synthesized from aminoacetonitrile and is typically obtained as chloride and bisulfate salts. It can also be produced in laboratory conditions by the reaction of aminoacetonitrile.
• Analysis Method: The solubility of MAAN in pure and binary solvents has been measured using a laser dynamic method. Various models, including the modified Apelblat equation, λh equation, NRTL model, Wilson model, Jouyban-Acree model, and Sun model, have been used to correlate the experimental solubility data. Thermodynamic properties such as dissolution enthalpy, entropy, and Gibbs energy have also been calculated to understand the dissolution process of MAAN in solvents.
• References: [1] Solubility and thermodynamic analysis of methyleneaminoacetonitrile in binary solvents from T?=?(278.15 to 323.15) K; DOI 10.1016/j.molliq.2019.03.069; [2] Solubility behaviour and thermodynamic analysis of methyleneaminoacetonitrile in binary (ethanol?+?water, ethanol?+?2-propanol, ethanol?+?n-butanol) solvents ; DOI 10.1016/j.jct.2019.06.009

Technology Process of Methyleneaminoacetonitrile

There total 8 articles about Methyleneaminoacetonitrile 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: 55.0%

potassium cyanide + formaldehyd (50-00-0,30525-89-4,61233-19-0) → methyleneaminoacetonitrile (109-82-0)

Guidance literature:

With ammonium chloride;

DOI:10.1002/jlcr.1602

Reference yield: 2.0%

1,3,5-tris(cyanomethyl)hexahydro-1,3,5-triazine (4560-87-6) → methyl isocyanate (593-75-9,685498-28-6) + methyleneaminoacetonitrile (109-82-0) + N-(methylimino)acetonitrile (59264-17-4)

Guidance literature:

With 3 A molecular sieve; at 220 ℃; under 0.1 Torr; Product distribution; flash vaccum pyrolysis at variation of temp.;

DOI:10.1002/hlca.19940770814

Reference yield:

1,3,5-tris(cyanomethyl)hexahydro-1,3,5-triazine (4560-87-6) → methyleneaminoacetonitrile (109-82-0)

Guidance literature:

at 190 ℃; Yield given;

upstream raw materials:

formaldehyd

sodium cyanide

1,3,5-tris(cyanomethyl)hexahydro-1,3,5-triazine

potassium cyanide

Downstream raw materials:

GlyOEt*HCl

iminodiacetonitrile

sarcosine

glycine

Refernces

• 1、 Dawadi, Prativa B. S.,Schulten, Els A. M.,Lugtenburg, Johan. "Synthesis of [3-13C]-, [4-13C]- and [11- 13C]-porphobilinogen". . p. 341 - 349. Retrieved 2009.
• 2、 Rinehart. "-". . p. 2794. Retrieved 1926.
• 3、 Dammel, Ralph,Bock, Hans. "Preparation of Monomeric Methyleneaminoacetonitrile H2C=N-CH2-CN in the Gas Phase". . p. 810 - 814. Retrieved 2007/10/02.