Synthesis of Tris(hydroxymethyl)nitromethane

Preparation of tris(hydroxymethyl)nitromethane (nitroisobutylglycerol)

Alternative Names: Tris(hydroxymethyl)nitromethane; 126-11-4; 2-(Hydroxymethyl)-2-nitropropane-1,3-diol; 2-(Hydroxymethyl)-2-nitro-1,3-propanediol; Cimcool wafers; Trimethylolnitromethane;

Preparation of tris(hydroxymethyl)nitromethane (nitroisobutylglycerol)

Preparation of tris(hydroxymethyl)nitromethane (nitroisobutylglycerol)

To prepare tris(hydroxymethyl)nitromethane one part of nitromethane is mixed with 4 parts of 40 % formaldehyde and about 1 g of potassium bicarbonate added. After a short time the condensation occurs with violent boiling. If the reaction does not occur the reaction mixture can be gently heated and then quickly cooled to temper the reaction. After evaporation in a vacuum the crude tris(hydroxymethyl)nitromethane remains as a mass of crystals. The yield of crude product is about theoretical. Tris(hydroxymethyl)nitromethane is then purified by sucking a little alcohol through it, or better to recrystallize from amyl alcohol or amyl acetate at 90° C. The yield is 70% of crude product, and has a melting point of 149° C.

Nitroglycerine and Nitroglycerine Explosives, by P Naoum, 240, 1928

IUPAC Name

2-(hydroxymethyl)-2-nitropropane-1,3-diol

InChI

InChI=1S/C4H9NO5/c6-1-4(2-7,3-8)5(9)10/h6-8H,1-3H2

InChI Key

OLQJQHSAWMFDJE-UHFFFAOYSA-N

Canonical SMILES

C(C(CO)(CO)[N+](=O)[O-])O

MeSH Synonyms

2-(hydroxymethyl)-2-nitro-1,3-propanediol, Tris Nitro

Depositor-Supplied Synonyms

Tris(hydroxymethyl)nitromethane, 126-11-4, 2-(Hydroxymethyl)-2-nitropropane-1,3-diol, 2-(Hydroxymethyl)-2-nitro-1,3-propanediol, Cimcool wafers, Trimethylolnitromethane, Tris nitro, Isobutylglycerol, nitro-, Nitroisobutylglycerol, Methane, trimethylolnitro-, Trihydroxymethylnitromethane, Nitrotris(hydroxymethyl)methane, 1,3-Propanediol, 2-(hydroxymethyl)-2-nitro-, 2-(Hydroxymethyl)-2-nitropropanediol, Caswell No. 495, 2-Nitro-2-(hydroxymethyl)-1,3-propanediol, Nitromethylidynetrimethanol, NSC 17675, 2-HYDROXYMETHYL-2-NITRO-1,3-PROPANEDIOL, 1,1,1-Tris(hydroxymethyl)nitromethane, HSDB 6810, OLQJQHSAWMFDJE-UHFFFAOYSA-N, EINECS 204-769-5, EPA Pesticide Chemical Code 083902, 2-Hydroxymethyl-2-nitropropane-1,3-diol, AI3-02259, 2-(Hydroxymethyl)-2 nitro-1,3-propanediol, ST51037689, DSSTox_CID_7034, 2-(hydroxymethyl)-2-nitro-propane-1,3-diol, WLN: WNX1Q1Q1Q, DSSTox_RID_78284, DSSTox_GSID_27034, 1, 2-(hydroxymethyl)-2-nitro-, 1,1-Tris(hydroxymethyl)nitromethane, Tris(hydroxymethyl-13C)nitromethane, CAS-126-11-4, Nitrotrimethylolmethane, ACMC-1BUIG, AC1L1LFE, trishydroxymethylnitromethane, UNII-3E794G4ZRB, SCHEMBL22312, KSC176A3N, 108189_ALDRICH, 3E794G4ZRB, tris(hydroxymethyl) nitromethane, Jsp001671, CHEMBL1895497, CTK0H6036, EBD4933, NSC2344, tris(hydroxymrthyl) nitromemethane, MolPort-000-882-277, NSC-2344, NSC17675, ZINC1640851, Tox21_200441, Tox21_300295, ANW-18580, NSC-17675, ZINC01640851, AKOS000278326, S.S.T sump saver tablets (Salt/Mix), MCULE-8637892145, NE10485, TRA0034892, NCGC00164036-01, NCGC00164036-02, NCGC00164036-03, NCGC00254029-01, NCGC00257995-01, AJ-28580, AK116035, AN-22971, CJ-26432, OR019948, OR188957, OR211087, OR211088, SC-62273, DB-041809, LS-120502, RT-001176, TL8000661, FT-0608817, ST24027631, V0537, EN300-17934, A805508, R601737, I14-0991, 3B3-030146, 2-Hydroxymethyl-2-Nitro-1,3-Propanediol (Tris(hydroxymethyl)nitromethane ), 2-hydroxymethyl-2-nitro-1,3-propanediol(tris(hydroxymethyl)nitromethane)

Removed Synonyms

CID31337, H0271, 10314-98-4

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